There’s something irresistibly delightful about combining bright, tropical pineapple flavors with the comforting sweetness of sugar cookies, and that’s exactly what the Pineapple Upside Down Sugar Cookies Recipe brings to your kitchen. Imagine biting into a soft, buttery cookie crowned with a jewel-like pineapple slice and a cheerful maraschino cherry, each nibble bursting with a perfect balance of tangy fruitiness and rich caramelized sweetness. This recipe transforms the nostalgic charm of pineapple upside down cake into portable, shareable cookies that are just as eye-catching as they are scrumptious. Whether you’re craving a fun summer treat or a unique twist on classic cookies, this recipe will become your new favorite go-to for impressing friends and family.
Ingredients You’ll Need
Getting started on the Pineapple Upside Down Sugar Cookies Recipe is straightforward, thanks to a list of classic baking staples and a few special touches. Each ingredient plays a key role to build the buttery, tender dough and those signature caramelized pineapple-topped bites you’ll love.
- 1 cup butter, room temperature: This forms the rich, creamy base of the cookie dough for tenderness and flavor.
- 1 ½ cups granulated sugar: Sweetens the dough, making every bite satisfying.
- 2 eggs: Help bind everything together and add moisture to the dough.
- 2 tsp vanilla extract: Infuses the cookies with warm, aromatic depth.
- ½ cup sour cream: Keeps the cookies extra moist and adds a subtle tang that balances sweetness.
- 3 cups all-purpose flour: The essential structure for the cookie’s chewy yet tender texture.
- 1 tsp baking powder: Gives a slight rise to keep the cookies light.
- 1 tsp cornstarch: Contributes to the soft, melt-in-your-mouth quality.
- ½ tsp salt: Enhances all the flavors, preventing the cookie from being overly sweet.
- 13 canned pineapple slices: The star of the show, adding juicy tropical flavor and visual appeal.
- 13 maraschino cherries: Add bright color and a sweet pop with every bite.
- ½ cup butter, melted: Used in the brown sugar topping for that luscious caramel effect.
- 1 cup light brown sugar, packed: Combines with melted butter to create the classic pineapple upside down cookie base.
How to Make Pineapple Upside Down Sugar Cookies Recipe
Step 1: Prepare the Pan and Topping
Start by mixing the melted butter with the light brown sugar until smooth and fully combined. Spoon about 1 tablespoon of this brown sugar mixture evenly into the bottom of each cavity of your prepared cookie pan or muffin tin. This is the magic layer that will caramelize beautifully during baking, giving your cookies that signature golden crust. Then, gently place a pineapple slice atop each portion of brown sugar. Center a maraschino cherry right in the middle of each pineapple slice to create that vibrant, classic look that’s so inviting.
Step 2: Make the Cookie Dough
In a large mixing bowl, cream together the room temperature butter and granulated sugar until fluffy and light in color—this will ensure a tender cookie. Beat in the eggs one at a time, followed by the vanilla extract and sour cream, mixing until everything is perfectly smooth. In a separate bowl, whisk together the all-purpose flour, baking powder, cornstarch, and salt. Gradually add the dry ingredients to the wet mixture, folding just until combined to avoid over-mixing, which can toughen the cookies.
Step 3: Assemble and Bake
Carefully spoon about 2 tablespoons of cookie dough on top of each pineapple slice in the pan, spreading gently to cover but without pushing too hard to avoid disturbing the fruit topping. Pop the pan in a preheated oven at 350°F (175°C) and bake for around 25 to 30 minutes or until the cookies are set and lightly golden on top. Once baked, allow the cookies to cool for a few minutes before carefully inverting the pan onto a cooling rack—this reveals the beautiful pineapple upside down topping as the cookie base.
How to Serve Pineapple Upside Down Sugar Cookies Recipe
Garnishes
These cookies are stunning on their own, but a little garnish can elevate their presentation even further. Consider a light dusting of powdered sugar for a snowy effect or a drizzle of melted white chocolate to add extra sweetness and elegance. Fresh mint leaves on the side also add a pop of green and a fresh aroma that pairs wonderfully with the tropical pineapple.
Side Dishes
Pair these cookies with a scoop of vanilla bean ice cream or a dollop of whipped cream to create a simple yet indulgent dessert experience. They also work well alongside a refreshing fruit salad or a tangy citrus sorbet, which complements the pineapple’s natural brightness and balances the cookie’s rich buttery flavors.
Creative Ways to Present
For a festive party or gathering, arrange the cookies on a large platter lined with tropical leaves for an island-inspired theme. You can also serve them individually on small dessert plates topped with a slice of fresh pineapple and a cherry for an extra special touch. Wrapping each cookie in clear cellophane tied with a colorful ribbon makes for perfect edible favors that guests will adore.
Make Ahead and Storage
Storing Leftovers
Once completely cooled, store your Pineapple Upside Down Sugar Cookies in an airtight container at room temperature for up to 3 days. This keeps them soft while maintaining the delicate balance of moist pineapple and crisp edges. If you want to keep them fresh a little longer, refrigerate but allow them to come to room temperature before serving.
Freezing
You can freeze these cookies either before or after baking. For unbaked dough, portion cookie rounds onto a baking sheet and freeze until firm before transferring them to a freezer-safe bag. For fully baked cookies, place parchment paper between layers in an airtight container and freeze for up to 2 months. Thaw at room temperature when ready to enjoy.
Reheating
To revive that just-baked warmth, gently heat the cookies in an oven preheated to 300°F (150°C) for 5 to 7 minutes. This helps melt the caramel topping slightly and refreshes the cookie’s soft texture wonderfully. Avoid microwaving as it may make the cookies too soft or soggy.
FAQs
Can I use fresh pineapple instead of canned?
Absolutely! Fresh pineapple slices work beautifully and add a lovely natural sweetness and texture. Just be sure to slice them evenly and pat dry to prevent extra moisture affecting the cookie dough.
Do I have to use maraschino cherries?
Maraschino cherries add both color and sweetness, but you can substitute with fresh cherries or even small pieces of dried cherries if preferred. Adjust placement carefully to maintain the classic look.
How do I know when the cookies are done baking?
The cookies should be set around the edges and lightly golden on top. When gently pressed, they shouldn’t feel doughy. A toothpick inserted into the side (not the fruit) should come out clean or with just a few crumbs attached.
Can I make the dough ahead of time?
Yes, the dough can be made a day in advance and kept tightly wrapped in the fridge. This actually enhances flavor and makes handling easier when you’re ready to bake.
What if I don’t have a muffin tin to bake them in?
You can use a similar-sized baking pan lined with silicone muffin cups, or form small cookie mounds on a flat sheet and place pineapple slices and cherries carefully on top, though the caramel effect will be a bit different.
Final Thoughts
If you’re looking to brighten up your cookie rotation with something enchanting and just a bit nostalgic, give the Pineapple Upside Down Sugar Cookies Recipe a try. It’s the kind of recipe that sparks smiles and brings a little sunshine to any occasion. Once you experience that burst of juicy pineapple, tender cookie, and sweet cherry goodness, you might find yourself making these again and again to share that joy with everyone you love.
Print
Pineapple Upside Down Sugar Cookies Recipe
- Prep Time: 20 minutes
- Cook Time: 20 minutes
- Total Time: 40 minutes
- Yield: 13 servings
- Category: Dessert
- Method: Baking
- Cuisine: American
Description
This Pineapple Upside Down Sugar Cookies recipe combines the classic flavors of a pineapple upside down cake with the convenience and portability of a cookie. Soft, buttery sugar cookie dough baked atop a luscious caramelized pineapple and cherry topping makes for a delightful dessert or snack perfect for any occasion.
Ingredients
For the Dough
- 1 cup butter, room temperature
- 1 ½ cups granulated sugar
- 2 eggs
- 2 tsp vanilla extract
- ½ cup sour cream
- 3 cups all-purpose flour
- 1 tsp baking powder
- 1 tsp cornstarch
- ½ tsp salt
For the Topping
- 13 canned pineapple slices
- 13 maraschino cherries
- ½ cup butter, melted
- 1 cup light brown sugar, packed
Instructions
- Prepare the Pan and Topping: Preheat your oven and grease a muffin or cupcake pan. Spoon about 1 tablespoon of the melted butter and brown sugar mixture into the bottom of each cavity, spreading it evenly to cover the base.
- Add Pineapple and Cherries: Place one canned pineapple slice on top of the brown sugar mixture in each cavity. Center a maraschino cherry in the middle of each pineapple slice for a classic look and burst of flavor.
- Make the Dough: In a large bowl, cream the room temperature butter with granulated sugar until light and fluffy. Beat in eggs one at a time, then add vanilla extract and sour cream, mixing well.
- Combine Dry Ingredients: In a separate bowl, whisk together the all-purpose flour, baking powder, cornstarch, and salt. Gradually add the dry ingredients to the wet ingredients, mixing until a soft dough forms.
- Assemble the Cookies: Scoop portions of the dough and gently place them over the pineapple and cherry topping in each cavity, spreading slightly to cover the fruit but not pressing too hard to keep the upside down effect.
- Bake the Cookies: Bake the assembled cookies in the preheated oven until golden around the edges and set in the center, approximately 18–22 minutes.
- Cool and Serve: Allow the cookies to cool in the pan for about 5 minutes. Then carefully invert the pan onto a cooling rack or serving plate so the pineapple and cherry topping are displayed on top. Let cool completely before serving.
Notes
- Make sure the butter for the dough is at room temperature for easier creaming and a smoother dough.
- Using a standard muffin pan helps create perfectly sized cookies with the classic pineapple upside down presentation.
- If canned pineapple slices are too large for your pan, cut them in half.
- Chilling the dough before baking is optional but can help prevent spreading.
- Be careful when inverting the pan to avoid breaking the cookies.
